Triazoles

Some common heterocyclic compound, 74205-82-6, name is (1H-1,2,4-Triazol-1-yl)methanol, molecular formula is C3H5N3O, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Product Details of 74205-82-6

Step 2. Preparation of 1-(chloromethyl)-1H-1,2,4-triazole To a solution of (1H-1,2,4-triazol-1-yl)methanol (1.0 g, 10.09 mmol) in dichloroethane (20 ml) thionyl chloride (1.105 ml, 15.14 mmol) was added and the reaction mixture was stirred at 100 C. for 4 hours. The reaction mixture was cooled to 30 C., poured into H2O (25 mL) and extracted with dichloromethane (3*20 mL). The combined organic layers was washed with H2O (50 mL) & brine solution (50 mL), dried over Na2SO4 and evaporated in rotavapor under vacuum to yield 1-(chloromethyl)-1H-1,2,4-triazole (0.570 g, 48%) as brown liquid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 74205-82-6, its application will become more common.

Reference:
Patent; CADILA HEALTHCARE LIMITED; DESAI, Ranjit C.; PINGALI, Harikishore; (40 pag.)US2016/83380; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 23579-79-5,Some common heterocyclic compound, 23579-79-5, name is 3,5-Dibromo-1-methyl-1H-1,2,4-triazole, molecular formula is C3H3Br2N3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

a) 5-Bromo-2-methyl-2H-[ 1 ,2,4]triazole-3-carbaldehyde To a solution of 3,5-dibromo-l-methyl-lH-l,2,4-triazole (500 mg, 2.08 mmol, Eq: 1.00) in tetrahydrofuran (5 ml) was added dropwise at -45 C under argon atmosphere n-butyllithium 1.6 M in hexane (1.56 ml, 2.49 mmol, Eq: 1.2). The resulting mixture was stirred for 30 minutes at -45C and was then cooled to -70C. Then dimethyl formamide (197 mg, 209 mu, 2.7 mmol, Eq: 1.3) wass added dropwise. After 15 minutes the cooling bath was removed and the mixture was allowed to reach 25 C. The mixture was stirred for additional 2 hours at 25 C. The mixture was poured on water and extracted twice with ethyl acetate, the organic layers were combined, washed with water and brine, dried over magnesium sulfate, filtrated and evaporated, affording 5-bromo-2-methyl-2H-[l,2,4]triazole-3-carbaldehyde (218 mg / 55.3 %) as an orange semi solid. MS: m/e= 189 (M+H+)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dibromo-1-methyl-1H-1,2,4-triazole, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; FLOHR, Alexander; GROEBKE ZBINDEN, Katrin; KUHN, Bernd; LERNER, Christian; RUDOLPH, Markus; SCHAFFHAUSER, Herve; WO2013/178572; (2013); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 58910-25-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 58910-25-1, name is 4-Ethyl-3-methyl-1H-1,2,4-triazol-5(4H)-one belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

After dissolving 4-ethyl-5-methyl-2,4-dihydro[1,2,4]triazol-3-one (CAS 58910-25-1) (2.00 g) in N,N-dimethylformamide (5 ml), sodium iodide (235 mg), sodium hydride (60% in oil) (238 mg) and (S)-(+)-epichlorhydrin (2.48 ml) were added and the mixture was stirred at room temperature for one day. Water was added to the reaction mixture, and extraction was performed with dichloromethane and ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (540 mg).1H-NMR (400 MHz, CDCl3); delta 1.29 (t, J=7.2 Hz, 3H), 2.24 (s, 3H), 2.67 (dd, J=4.8, 2.8 Hz, 1H), 2.84 (t, J=4.8 Hz, 1H), 3.22-3.27 (m, 1H), 3.68 (q, J=7.2 Hz, 2H), 3.86 (dd, J=14.8, 5.6 Hz, 1H), 3.96 (dd, J=14.8, 4.4 Hz, 1H).

The synthetic route of 4-Ethyl-3-methyl-1H-1,2,4-triazol-5(4H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai R&D Management Co., Ltd.; US2009/270369; (2009); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 4923-01-7, A common heterocyclic compound, 4923-01-7, name is 5-Methyl-4H-1,2,4-triazol-3-amine, molecular formula is C3H6N4, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

3-methyl-1H-1,2,4-triazol-5-amine (4.7747 g, 48.7 mmol, 1 eq.) and 2- bromomalonaldehyde (8.08 g, 53.5 mmol, 1.1 eq.) were dissolved in AcOH (50 ml) and heated15 at 60 C for 18 hours under inert conditions. The reaction mixture was concentrated under vacuo, then the crude material was redissolved in EtOAc and filtered. The filtrate was combined with NaHCO3, and the aqueous layer was extracted with EtOAc (x3). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. The crude material was absorbed onto silica and purified by column chromatography (Si02, 100% DCM, then 98:2 DCM:MeOH)20 to give 6-bromo-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidine (2.22g, 21%, mlz: 215.1 [M+H]+) as an off-white solid.

The synthetic route of 4923-01-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GILLESPIE, Robert Jack; HASANE, Ratni; SARIE, Jerome Charles; (89 pag.)WO2016/184832; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 288-36-8,Some common heterocyclic compound, 288-36-8, name is 1H-1,2,3-Triazole, molecular formula is C2H3N3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of 2-iodobenzoic acid (3.0 g, 12.1 mmol) in DMF was added 1,2,3- triazole (1.5 g, 21.7 mmol), Cs2C03(7.1 g, 21.7 mmol), Cul (114 mg, 0.6 mmol), and trans-N,K- dimethylc)rclohexane-l,2-diamine (310 mg, 2.2 mmol). After heating at 120 C for 10 min in a microwave reactor, the mixture was cooled to room temperature, diluted with EtOAc, and filtered through Celite. The filtrate was concentrated in vacuo and the crude residue was purified by silica gel chromatography (MeOH in DCM with 0.1% AcOH) to give Intermediate H as the faster eluting isomer. 1H NMR (DMSO-d6 , 500MHz) delta 13.05 (brs, 1 H), 8.12 (s, 2H), 7.81-7.52 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1H-1,2,3-Triazole, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; REGER, Thomas, S.; SKUDLAREK, Jason, W.; (0 pag.)WO2016/85784; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 107534-96-3, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 107534-96-3, name is 3-((1H-1,2,4-Triazol-1-yl)methyl)-1-(4-chlorophenyl)-4,4-dimethylpentan-3-ol, This compound has unique chemical properties. The synthetic route is as follows.

Complex [Pd2Cl4L2] (III) was synthesized at a predetermined ratio Pd(II) : L = 1 : 1. To palladium(II)chloride (0.20 g, 1.13 mmol) placed into a 25mL pear-shaped flask with a reflux condenser, acetonitrile(10 mL) was added, and the resulting mixture was refluxed on a sand bath until the salt was completely dissolved. The formed yellow-brown trans-(bisacetonitrile)dichloropalladium solution was cooled to 60, there upon reagent L (0.35 g, 1.13 mmol) was added. The color of the solution changed to light yellow. Acetonitrile was removed on a rotary evaporator, and the separated substance was washed with hexane and dried. The yield was 95%.

The chemical industry reduces the impact on the environment during synthesis 3-((1H-1,2,4-Triazol-1-yl)methyl)-1-(4-chlorophenyl)-4,4-dimethylpentan-3-ol. I believe this compound will play a more active role in future production and life.

Reference:
Article; Khisamutdinov; Shitikova; Anpilogova; Golubyatnikova; Mulagaleev; Murinov; Russian Journal of Inorganic Chemistry; vol. 60; 5; (2015); p. 638 – 646; Zh. Neorg. Khim.; vol. 60; 5; (2015); p. 710 – 718,9;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 288-36-8, name is 1H-1,2,3-Triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C2H3N3

A solution of 5-bromo-2-chloro-6-methylnicotinonitrile (8.5 g, 36.7 mmol), 2H-1,2,3-triazole (5.07 g, 73.4 mmol) and potassium carbonate (15.2 g, 110.2 mmol) in acetonitrile (150 mL) was stirred at 40 C. overnight. The mixture was filtered and washed with ethyl acetate (200 mL*3). The filtrate was concentrated to afford a crude product. The crude product was purified by flash column chromatography over silica gel (eluent: petroleum ether/ethyl acetate from 100/0 to 30/70). The eluent was collected and the solvent was concentrated under reduced pressure to give the product as a yellow solid (7 g, 72% yield). 1H NMR (400 MHz, DMSO-d6) delta ppm 2.71 (s, 3H), 8.31 (s, 2H), 8.90 (s, 1H). LC-MS: (ES, m/z): [M+1]+ 264.0

The synthetic route of 288-36-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 626248-56-4, name is 3-(2H-1,2,3-Triazol-2-yl)aniline, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 626248-56-4

Reactor A was charged with solid ethyl 4-chloro-2-methylthio-5-pyrimidine carboxylate (1.00kg). Reactor A was then charged with absolute ethanol (5.OOL, 4.0kg). Reactor A was then charged with triethylamine (0.62L, 0.45kg). The content of Reactor A was then cooled to about 20 C. Reactor A was then charged 3-amino-N-phenyl-triazole (0.70kg). The reaction mixture was slowly heated to 30-40 C over about 1 hour to give an off white suspension. The contents of Reactor A was stirred between 30-40 C for about 6 hours. 8) Sample solution for ion pair chromatography for less than 1% (area) by HPLC of ethyl 4-chloro-2-methylthio-5-pyrimidine carboxylate. If the sample result complies with criterion proceed to the next step, otherwise agitate for an additional 2 hours between 30-40C and sample again. The reaction mixture generally turns into almost unmixable slurry toward the end of the reaction. The contents of Reactor A was cooled to about 20 C. Tap water (8.OOL, 8.00kg) was charged into Reactor B and the temperature of the contents of Reactor B was adjusted to about 15 C. The contents of Reactor B was charged into Reactor A, while maintaining the temperature at about 15C in Reactor A. The contents of Reactor A was stirred for about 30 minutes at about 15C. The contents of Reactor A was filtered using a filter cloth of about 8im or smaller to accommodate the particle size, or an oyster-style filter with a 3 – 5 im polypropylene filter cloth. Reactor B was charged with tap water (10.OOL, 10.00kg) and half the contents of Reactor B was charged to the filter to wash the solids. The remaining contents of Reactor B was charged to the filter to wash the solids. Reactor B was charged with methyl tert-butyl ether (3.OOL, 2.22kg). The contents of Reactor B was then charged to the filter to wash the solids. The contents of the filter was dried under vacuum such as in a vacuum tray dryer at about 55 C for about 12 hours, until the water (by Karl Fischer) is < 1 % w/w.The title compound was prepared according to Process Example 1 starting with 25.0 kg of ethyl 4-chloro-2-methylthio-5-pyrimidine, 11.25 kg triethylamine, 100 kg absolute ethanol and 17.5 kg 3-amino-N-phenyl-triazole. A 90.4% yield of the title compound was obtained. According to the analysis of related databases, 626248-56-4, the application of this compound in the production field has become more and more popular. Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; PANDEY, Anjali; WO2014/152768; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1186050-58-7, name is 2-Fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 2-Fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid

Step A: (1 S,6R)-tert-Butyl 8-(2-fluoro-6-(2H-1 ,2,3-triazol-2-yl)benzoyl)-3,8-diazabicyclo[4.2.0]octane-3-carboxylate. To 2-fluoro-6-(2H-1 ,2,3-triazol-2- yl)benzoic acid (406 mg, 1 .5 mmol) in PhCH3 (5ml_) was added SOCI2 (1 17 u?_, 1 .6 mmol). The flask was heated with an oil bath to 50 C for 1 h. To (1 S,6R)- tert-butyl 3,8-diazabicyclo[4.2.0]octane-3-carboxylate (260 mg, 1 .3 mmol) and Na2CO3 (519 mg, 4.9 mmol) in PhCH3 (5ml_) and H2O (5mL) at 0 C was added the above solution dropwise. The reaction was allowed to warm slowly to rt and stir for 15h and extracted with DCM (2 X). The combined organics were dried (Na2SO4). Purification via silica gel chromatography (1 -7% 2MNHs/MeOH in CH2CI2) gave 335 mg (68%) of the title compound. MS (ESI) mass calcd. C2oH24FN5O3, 401 .44; m/z found 346.1 [M-C(CH3)3]+

The synthetic route of 1186050-58-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; WO2011/50202; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 27808-16-8, The chemical industry reduces the impact on the environment during synthesis 27808-16-8, name is 4-Methyl-1H-1,2,3-triazole, I believe this compound will play a more active role in future production and life.

Example 74 N-((1S)-2-hydroxy-2-methyl-1-(4-(trifluoromethoxy)phenyl)propyl)-5-(4-methyl-1H-1,2,3-triazol-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide A solution of (S)-5-chloro-N-(2-hydroxy-2-methyl-1-(4-(trifluoromethoxy)phenyl)propyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (200 mg), 4-methyl-1H-1,2,3-triazole (46.5 mg) and potassium carbonate (97 mg) in N,N-dimethylformamide (2 mL) was stirred at 80 C. for 2 hr. Water was added to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was fractionated by HPLC (C18, mobile phase: water/acetonitrile (0.1% TFA-containing system)). The obtained fraction with a shorter retention time was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was crystallized from hexane/ethyl acetate to give the title compound (37.5 mg).MS (API+): [M+H]+476.2.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Methyl-1H-1,2,3-triazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; Kawasaki, Masanori; Mikami, Satoshi; Nakamura, Shinji; Negoro, Nobuyuki; Ikeda, Shuhei; Nomura, Izumi; Ashizawa, Tomoko; Imaeda, Toshihiro; Seto, Masaki; Sasaki, Shigekazu; Marui, Shogo; Taniguchi, Takahiko; (130 pag.)US2016/159808; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics